(2S,3R)-1,2-dihydro-6-tert-butyldiphenylsilyloxy-hexan-3-yl 2-(phenylthio)acetate

Base Information

• Chemical Name: (2S,3R)-1,2-dihydro-6-tert-butyldiphenylsilyloxy-hexan-3-yl 2-(phenylthio)acetate
• CAS No.: 920502-52-9
• Molecular Formula: C₃₀H₃₈O₅SSi
• Molecular Weight: 538.78
• Mol file: 920502-52-9.mol

Synonyms:(2S,3R)-1,2-dihydro-6-tert-butyldiphenylsilyloxy-hexan-3-yl 2-(phenylthio)acetate

Chemical Property of (2S,3R)-1,2-dihydro-6-tert-butyldiphenylsilyloxy-hexan-3-yl 2-(phenylthio)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-1,2-dihydro-6-tert-butyldiphenylsilyloxy-hexan-3-yl 2-(phenylthio)acetate

There total 1 articles about (2S,3R)-1,2-dihydro-6-tert-butyldiphenylsilyloxy-hexan-3-yl 2-(phenylthio)acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

(phenylthio)acetic acid (103-04-8) + (2S,3S)-(3-(3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propyl)-2-oxiranyl)methan-1-ol (127379-30-0) → (2S,3R)-1,2-dihydro-6-tert-butyldiphenylsilyloxy-hexan-3-yl 2-(phenylthio)acetate (920502-52-9)

Guidance literature:

With titanium(IV) isopropylate; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.jorganchem.2006.08.021

Reference yield: 74.0%

(2S,3R)-1,2-dihydro-6-tert-butyldiphenylsilyloxy-hexan-3-yl 2-(phenylthio)acetate (920502-52-9) + trimethyl phosphonoacetate (5927-18-4) → methyl (4R)-4-[(phenylthio)-acetoxy]-7-tert-butyldiphenylsilyloxy-hepten-2(E)-oate (920502-53-0)

Guidance literature:

(2S,3R)-1,2-dihydro-6-tert-butyldiphenylsilyloxy-hexan-3-yl 2-(phenylthio)acetate; With sodium periodate; tetrabutylammonium periodite; In methanol; water; at 20 ℃; for 1h;

trimethyl phosphonoacetate; With sodium hydride; In benzene; for 0.5h;

DOI:10.1016/j.jorganchem.2006.08.021

Reference yield:

(2S,3R)-1,2-dihydro-6-tert-butyldiphenylsilyloxy-hexan-3-yl 2-(phenylthio)acetate (920502-52-9) → (3S,3aR,8aR)-3-phenylthio-3a,4,8,8a-tetrahydro-cycloheptenfuran-2(3H)-one

Guidance literature:

Multi-step reaction with 8 steps

1.1: NaIO₄; tetrabutylammonium periodate / methanol; H₂O / 1 h / 20 °C

1.2: 74 percent / sodium hydride / benzene / 0.5 h

2.1: 95 percent / sodium hydride / dimethylformamide / 4 h

3.1: 90 percent / NaOH / tetrahydrofuran; H₂O

4.1: 86 percent / BH₃*SMe₂ / tetrahydrofuran

5.1: SO₃*pyridine / CH₂Cl₂

5.2: 78 percent / KHMDS / tetrahydrofuran

6.1: 92 percent / tetra-butylammonium fluoride / tetrahydrofuran / 20 °C

7.1: SO₃*pyridine / CH₂Cl₂

7.2: 80 percent / KHDMS / tetrahydrofuran

8.1: 89 percent / second generation Grubbs catalyst / CH₂Cl₂ / 40 °C

With sodium hydroxide; sodium periodate; pyridine-SO₃ complex; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; sodium hydride; tetrabutylammonium periodite; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.jorganchem.2006.08.021

upstream raw materials:

(phenylthio)acetic acid

(2S,3S)-(3-(3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propyl)-2-oxiranyl)methan-1-ol

Downstream raw materials:

methyl (4R)-4-[(phenylthio)-acetoxy]-7-tert-butyldiphenylsilyloxy-hepten-2(E)-oate

(3S,4R,5R)-4-allyl-5-(3-butenyl)-3-phenylthio-dihydrofuran-2-one

(3S,4R,5R)-4-allyl-5-(3-hydroxypropyl)-3-phenylthio-dihydrofuran-2-one

(3S,4R,5R)-4-allyl-3-phenylthio-5-(3-tert-butyldiphenylsilyloxy)propyl-dihydrofuran-2-one